2,2'-Dihydroxy-N,N'-(ethane-1,2-di-yl)di-benzamide.

The asymmetric unit of the title compound, C(16)H(16)N(2)O(4), contains one half-mol-ecule, the whole mol-ecule being generated by an inversion center located at the mid-point of the C-C bond of the central ethane group. An intra-molecular O-H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, mol-ecules are connected via N-H⋯O hydrogen bonds, generating infinite chains along [1-10].

Related literature

For the synthesis of bis­amides, see: Apurba et al. (2002 ▶); Fry et al. (2010 ▶). For similar bis­amide crystal structures, see: Booysen et al. (2009 ▶). For applications of bis­amides as catalysts, see: Maurya et al. (2003 ▶); Liu et al. (2011 ▶).

Experimental

Crystal data

C16H16N2O4

M = 300.31

Triclinic,

a = 4.6311 (3) Å

b = 5.0435 (3) Å

c = 15.2957 (9) Å

α = 89.091 (4)°

β = 83.315 (4)°

γ = 85.956 (4)°

V = 353.94 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.34 × 0.24 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: gaussian (SADABS; Bruker, 2009 ▶) T min = 0.966, T max = 0.989

9142 measured reflections

1535 independent reflections

924 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.143

S = 1.01

1535 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051963/lr2096sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051963/lr2096Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051963/lr2096Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H16N2O4	Z = 1
Mr = 300.31	F(000) = 158
Triclinic, P1	Dx = 1.409 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.6311 (3) Å	Cell parameters from 1575 reflections
b = 5.0435 (3) Å	θ = 2.7–25.8°
c = 15.2957 (9) Å	µ = 0.10 mm−1
α = 89.091 (4)°	T = 296 K
β = 83.315 (4)°	Block, colourless
γ = 85.956 (4)°	0.34 × 0.24 × 0.11 mm
V = 353.94 (4) Å3

Bruker APEXII CCD diffractometer	1535 independent reflections
Radiation source: fine-focus sealed tube	924 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 27.1°, θmin = 2.7°
Absorption correction: gaussian (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.966, Tmax = 0.989	k = −6→6
9142 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0644P)2 + 0.0596P] where P = (Fo2 + 2Fc2)/3
1535 reflections	(Δ/σ)max < 0.001
100 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.4041 (3)	1.1108 (3)	0.79344 (10)	0.0718 (5)
H1	0.4677	1.0900	0.8411	0.108*
O2	0.7318 (3)	0.9317 (3)	0.90207 (9)	0.0629 (5)
N	1.0113 (3)	0.5534 (3)	0.87856 (10)	0.0507 (5)
H0	1.0709	0.4248	0.8433	0.061*
C1	0.7459 (4)	0.7361 (3)	0.76153 (11)	0.0426 (5)
C2	0.5357 (4)	0.9263 (4)	0.73646 (12)	0.0496 (5)
C3	0.4584 (5)	0.9234 (5)	0.65190 (15)	0.0676 (6)
H3	0.3184	1.0495	0.6352	0.081*
C4	0.5845 (5)	0.7384 (4)	0.59253 (14)	0.0649 (6)
H4	0.5312	0.7405	0.5357	0.078*
C5	0.7895 (5)	0.5493 (5)	0.61620 (14)	0.0655 (6)
H5	0.8742	0.4220	0.5760	0.079*
C6	0.8674 (5)	0.5507 (4)	0.69979 (13)	0.0589 (6)
H6	1.0068	0.4226	0.7156	0.071*
C7	0.8293 (4)	0.7466 (4)	0.85175 (12)	0.0448 (5)
C8	1.1112 (4)	0.5513 (4)	0.96491 (12)	0.0523 (5)
H8A	1.1517	0.7304	0.9796	0.063*
H8B	1.2913	0.4402	0.9636	0.063*

	U11	U22	U33	U12	U13	U23
O1	0.0882 (11)	0.0606 (9)	0.0622 (9)	0.0348 (8)	−0.0120 (8)	−0.0122 (7)
O2	0.0780 (10)	0.0543 (9)	0.0545 (9)	0.0202 (7)	−0.0125 (7)	−0.0214 (7)
N	0.0591 (10)	0.0484 (10)	0.0439 (9)	0.0123 (8)	−0.0115 (7)	−0.0116 (7)
C1	0.0458 (10)	0.0388 (10)	0.0426 (10)	0.0022 (8)	−0.0050 (8)	−0.0043 (8)
C2	0.0569 (11)	0.0402 (10)	0.0501 (11)	0.0053 (9)	−0.0049 (9)	−0.0011 (9)
C3	0.0806 (15)	0.0620 (14)	0.0601 (13)	0.0147 (12)	−0.0198 (12)	0.0036 (11)
C4	0.0828 (16)	0.0679 (15)	0.0459 (12)	−0.0029 (12)	−0.0165 (11)	−0.0007 (11)
C5	0.0820 (15)	0.0642 (14)	0.0490 (12)	0.0113 (12)	−0.0094 (11)	−0.0158 (10)
C6	0.0696 (13)	0.0567 (13)	0.0488 (12)	0.0176 (10)	−0.0111 (10)	−0.0120 (10)
C7	0.0458 (10)	0.0420 (10)	0.0456 (10)	0.0040 (8)	−0.0041 (8)	−0.0085 (8)
C8	0.0540 (11)	0.0563 (12)	0.0477 (11)	0.0058 (9)	−0.0154 (8)	−0.0091 (9)

O1—C2	1.349 (2)	C3—C4	1.365 (3)
O1—H1	0.8206	C3—H3	0.9300
O2—C7	1.245 (2)	C4—C5	1.372 (3)
N—C7	1.334 (2)	C4—H4	0.9300
N—C8	1.449 (2)	C5—C6	1.369 (3)
N—H0	0.8600	C5—H5	0.9300
C1—C6	1.383 (2)	C6—H6	0.9300
C1—C2	1.400 (3)	C8—C8i	1.511 (4)
C1—C7	1.478 (2)	C8—H8A	0.9700
C2—C3	1.382 (3)	C8—H8B	0.9700
C2—O1—H1	109.5	C6—C5—C4	119.07 (19)
C7—N—C8	122.58 (15)	C6—C5—H5	120.5
C7—N—H0	118.6	C4—C5—H5	120.5
C8—N—H0	118.8	C5—C6—C1	122.21 (18)
C6—C1—C2	117.95 (17)	C5—C6—H6	118.9
C6—C1—C7	123.62 (16)	C1—C6—H6	118.9
C2—C1—C7	118.42 (15)	O2—C7—N	120.36 (17)
O1—C2—C3	119.21 (17)	O2—C7—C1	120.87 (16)
O1—C2—C1	121.37 (17)	N—C7—C1	118.78 (15)
C3—C2—C1	119.42 (17)	N—C8—C8i	112.0 (2)
C4—C3—C2	120.98 (19)	N—C8—H8A	109.2
C4—C3—H3	119.5	C8i—C8—H8A	109.2
C2—C3—H3	119.5	N—C8—H8B	109.2
C3—C4—C5	120.4 (2)	C8i—C8—H8B	109.2
C3—C4—H4	119.8	H8A—C8—H8B	107.9
C5—C4—H4	119.8
C6—C1—C2—O1	178.94 (18)	C2—C1—C6—C5	0.3 (3)
C7—C1—C2—O1	−2.0 (3)	C7—C1—C6—C5	−178.7 (2)
C6—C1—C2—C3	−0.3 (3)	C8—N—C7—O2	−1.8 (3)
C7—C1—C2—C3	178.77 (19)	C8—N—C7—C1	178.24 (17)
O1—C2—C3—C4	−179.4 (2)	C6—C1—C7—O2	173.61 (19)
C1—C2—C3—C4	−0.2 (4)	C2—C1—C7—O2	−5.4 (3)
C2—C3—C4—C5	0.6 (4)	C6—C1—C7—N	−6.5 (3)
C3—C4—C5—C6	−0.6 (4)	C2—C1—C7—N	174.55 (17)
C4—C5—C6—C1	0.2 (4)	C7—N—C8—C8i	80.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.76	2.495 (2)	148
N—H0···O1ii	0.86	2.21	2.993 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.76	2.495 (2)	148
N—H0⋯O1i	0.86	2.21	2.993 (2)	151

Symmetry code: (i) .